Hypervalent iodine-mediated formation of S-S, C-S, C-O, and C-N bonds

Di(4-nitrobenzoyloxy)iodo]benzene (1), a hypervalent iodine compound, is easy to prepare and stable as a solid, and was shown to be a useful functional group transforming agent in this report. Oxidative synthesis of symmetrical disulfides from thiols in the presence of compound 1 alone was performed in 58-100% yields. Furthermore, ESI-MS demonstrated that premixing of 1 and Ph3P yields the corresponding acyloxyphosphonium, which can acylate thiols to produce thioesters in 69-100% yields. With the assistance of a mixture of 1 and Ph3P, hydroxy and amino groups were benzoylated to esters and amides, respectively, also in 9-100% yields.